Structure-activity relations in psychotomimetic phenylalkylamines

Structure–Activity Relationships of Phenylalkylamines as Agonist Ligands for 5‐HT2A Receptors

“…[67] Addition of a b-methyl group to the side chain has been found to reduce in vivo activity, and this applies to b-hydroxy and b-keto groups as well. [166,167] Interestingly, certain b-methoxy-substituted phenethylamines retain some potency in humans. [117,145] The poor ability of b-oxygenated agents to cross the blood-brain barrier and enter the CNS is thought to account for the reduced in vivo activity.…”

Synthesis of deuterium‐labelled standards of (±)‐DOM and (±)‐MMDA

“…Although DOM [7][8][9][10][11][12][13][14] and MMDA 15 (14). 15 Bromination of commercially available protocatechualdehyde 6 in acetic acid gave 3-bromo-protocatechualdehyde 7.…”

“…These were dried in vacuum until free from acetic acid. The product was purified by recrystallization using 50% ethanol, producing the product, 3-bromo-4,5-dihydroxybenzaldehyde 7 (1.50 g, 6.9 mmol Synthesis of 3-bromo-4,5-methylenedioxybenzaldehyde (8). To a solution of 3-bromo-4,5-dihydroxybenzaldehyde 7 (1.10 g, 5.1 mmol) in DMSO (3.6 ml) was added methylene iodide (0.87 ml, 10.8 mmol) followed by anhydrous potassium carbonate (2.00 g), which was heated at 1008C for 3 h. After it had returned to room temperature, it was added to water (100 ml), made strongly basic by the addition of sodium hydroxide, and extracted using dichloromethane.…”

Gold(III) Chloride‐Catalyzed Addition Reactions of Electron‐Rich Arenes to Methyl Vinyl Ketone

“…Recrystallization from diethyl ether afforded 20 as colorless crystals; yield: 229 mg (48%), mp 52 8C (Lit. [13] bp 118 ± 120 8C/0.1 Torr); 12 (s, 5H). The spectroscopic data were in accordance with the data in the literature.…”

“…The solvent was removed under vacuum at 50 8C (from 15 mbar to 0.2 mbar) and the residue purified by flash chromatography on silica gel (petroleum ether/tert-butyl methyl ether, 2 : 1; R f 0.27) to give 19 as colorless crystals; yield: 237 mg (99.5%), mp 64 8C (Lit. [13] bp 140 ± 142 8C/0.1 Torr); After 40 min at room temperature the reaction mixture was filtered through a small pad of silica (4 g) with additional 10 mL of acetonitrile as eluent. The solvent was removed under vacuum at 50 8C (from 15 mbar to 0.2 mbar) and the residue purified by flash chromatography on silica gel (petroleum ether/tert-butyl methyl ether, 2 : 1; R f 0.22).…”